Condensation product of naphthol, aldehyde, and dithio acid and method of preparing it



CONDENSATION PRODUCT OF NAPHTHOL, ALDEHYDE, AND DITHIO ACID AND METHOD OF PREPARING IT Albert F. Hardman, Akron, Ohio, assignor to Wingfoot Corporation, Wilmington, Del., a corporation of Delaware No Drawing. Original application November 23,

1940, Serial No.

366,883. Divided and this application August 30, 1941, Serial No. 409,100

8 Claims. (01. 260-345) This invention relates to new chemical com- Parts by pounds and the method of preparing them. The weight compounds may be used as accelerators of the Rubber 100.0 vulcanization of rubber. Sulfur 3.0

The compounds are formed by reacting (1) a Zinc oxide 5.0 naphthol, (2) an aldehyde and (3) a dithio acid, Accelerator .5 such as dithioacetic acid, dithiofuroic acid, a di- Diphenylguanidine .2

thionaphthoic acid or dithiobenzoic acid or its homologs, including dithio phenyl benzoic acid.

Instead of diphenylguanidine, ditolylgnanidine or any basic type accelerator may be used. The

As the aldehyde, paraformaldehyde (water-free) curing data obtained with samples employing is preferred. Formaldehyde may be used. The this formula were as follows; naphthol may be alpha or beta naphthol or a substituted derivative thereof. I I

Generally p g a catalyst is required for Cure in minutes, degrees F. Tensile Elongation M5%%I,I7I7HS the reaction. An alkaline or basic catalyst is used, and as it, must be soluble in the reaction j Z 61 965 8 mass an organic compound will be preferred, such Z2 '"j as hexamethylenetetramine, quinoline, piperi- 230 800 as dine, lutidine, quinaldine or dimethylaniline. 37 The invention will be further described in con- 29 This application is a division of my app1ica the ammpanymg example' tion Serial No. 366,883 filed November 23, 1940.

What I claim is: EXAMPLE 1. As a new product, R.CH2S.C(:S) R1 Where R The following compounds are mixed in the folis a naphthol group and S.C(:S)R1 is a dithio lowing proportions: acid D- Part by 2. As a new product, R.CH2S.C( :S)R1 where R weight is a naphthol group and -S.C(:S)R1 is a dithio 2-hydroxy-dithionaphthoic acid 39.0 naphthoic acid. Beta-naphthol 30.0 3. As a new product, R.CH2S.C( :S)P..1 Where R Paraformaldehyde 6.5 30 is a naphthol group and S.C(:S)R1 is dithio Toluene 215.0 furoic acid. Piperidine (as a catalyst) Trace S a new product, R.CH2S.C(:S)R1 where R is a naphthol group and S.C(:S) R1 is a dithio The ingredients are refluxed with a water trap benzoic acid. until about 3.5 to 4.0 parts by weight of water 5. The process which comprises reacting, in has been collected. The reacted mix is then filthe presence of a basic catalyst and at an eletered and the solvent evaporated. In one invated temperature, substantially equimolecular stance this yielded 50 parts by weight of orangeproportions of (1) a naphthol, (2) an aldehyde red crystals which melted at 142-3" C. from the group consisting of formaldehyde and Analysis: Sulfur found was 16.77 and 16.81%. paraformaldehyde and (3) a dithio acid. Calculated to C22H16O2S2, the sulfur equals 6. The process which comprises reacting, in 17.0%. The formula, therefore, appears to be: the presence of a basic catalyst and at an elevated temperature, substantially equimolecular Formula proportions of (l) a naphthol, (2) an aldehyde from the group consisting of formaldehyde and s pargformaldehyde and (3) a dithio naphthoic H 8.01 c-s- L- '7. The process which comprises reacting, in H the presence of a basic catalyst and at an ele- $11 on vated itemperature, substantially equimolecular propor ions of (1) a naphthol, (2) an aldeh de Other dithio acids, such as those above menf m the group consisting f f rm ldehyd 5 tioned may be si i reacted to Produce paraformaldehyde and (3) dithio furoic acid. prod having the general formula 8. The process which comprises reacting, in

5 the presence of a basic catalyst and at an elevated temperature, substantially equimolecular where R is a naphthol nucleus, and R1 may be proportions of (1) a naphthol, (2) an aldehyde aliphatic or tic, from the group consisting of formaldehyde and This accelerator was used for the acceleration paraformaldehyde and (3) a dithio benzoic acid. of rubber in the following formula: ALBERT F. HARDMAN. 

